15647-89-9Relevant academic research and scientific papers
Reaction of R-pulegone with P–H phosphonium salts
Fayzullin, Robert R.,Grigor'eva, Leysan R.,Khasiyatullina, Nadezhda R.,Mironov, Vladimir F.,Nemtarev, Andrey V.,Shemakhina, Mariya E.
, p. 700 - 702 (2021/01/12)
The reaction of the R-pulegone with P–H-phosphonium salts gives the corresponding 8-phosphonio-p-menthan-3-one salts with high regio- and stereoselectivity. The structure of salts was determined by NMR and IR spectroscopy, mass spectrometry and X-ray diffraction analysis.
Preparation, characterization, and theoretical study of nanoparticles of triphenylphosphonium tetrachloroaluminate(III) [P(C6H 5)3H]+[AlCl4]-
Ghammamy, Shahriar
, p. 390 - 394 (2013/05/22)
Triphenylphosphonium tetrachloroaluminate(III) [P(C6H 5)3H]+[AlCl4]-, TPPTCA, nanoparticle was synthesized by using triphenylphosphonium chloride addition to AlCl3 in the presence of surfactant. The product was characterized by spectroscopic and analytical methods such as 31P-NMR, FT-IR, XRD, SEM, and CHN. Theoretical calculations were used for the structural optimization of this compound. The structure of compound has been calculated and optimized by the density functional theory (DFT) based method at B3LYP/6-311G levels of theory, using the Gaussian 03 package of programs. The comparison between theory and experiment is made. On the base of the application of scanning electron microscopy is showed about 54 nm particle sizes. Copyright Taylor & Francis Group, LLC.
Process for Synthesis of (3S)- and (3R)-3-Hydroxy-Beta-Ionone, and Their Transformation to Zeaxanthin and Beta-Cryptoxanthin
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, (2009/12/27)
(3R)-3-Hydroxy-β-ionone and (3S)-3-hydroxy-β-ionone are two important intermediates in the synthesis of carotenoids with β-end group such as lutein, zeaxanthin, β-cryptoxanthin, and their stereoisomers. Among the various stereoisomers of these carotenoids, only (3R,3′R,6′R)-lutein, (3R,3′R)-zeaxanthin, and (3R)-β-cryptoxanthin are present in commonly consumed fruits and vegetables. There are 3 possible stereoisomers for zeaxanthin, these are: dietary (3R,3′R)-zeaxanthin (1), non-dietary (3S,3′S)-zeaxanthin (2), and non-dietary (3R,3′S;meso)-zeaxanthin (3) which is a presumed metabolite of dietary lutein. Dietary lutein as well as 1 and 3 are accumulated in the human macula and have been implicated in the prevention of age-related macular degeneration. (3R)-β-Cryptoxanthin (4) is also present in selected ocular tissues at a very low concentration whereas its enantiomer (3S)-β-cryptoxanthin (5) is absent in foods and human plasma. The present invention relates to a process for the synthesis of (3R)-3-hydroxy-β-ionone and its (3S)-enantiomer in high optical purity from commercially available (rac)-α-ionone. The key intermediate for the synthesis of these hydroxyionones is 3-keto-α-ionone ketal that was prepared from (rac)-α-ionone after protection of this ketone as a 1,3-dioxolane. Reduction of 3-keto-α-ionone ketal followed by deprotection, lead to 3-hydroxy-α-ionone that was transformed into (rac)-3-hydroxy-β-ionone by base-catalyzed double bond isomerization in 46% overall yield from (rac)-α-ionone. The racemic mixture of these hydroxyionones was then resolved by enzyme-mediated acylation in 96% ee. (3R)-3-Hydroxy-β-ionone and its (3S)-enantiomer were respectively transformed to (3R)-3-hydroxy-(β-ionylideneethyl)triphenylphosphonium chloride [(3R)—C15-Wittig salt] and its (3S)-enantiomer [(3S)—C15-Wittig salt] according to known procedures. Double Wittig condensation of these Wittig salts with commercially available 2,5-dimethylocta-2,4,6-triene-1,8-dial provided all 3 stereoisomers of zeaxanthin (1-3). Similarly, (3R)—C15-Wittig and its (3S)-enantiomer were each coupled with β-apo-12′-carotenal to yield 4 and 5.
Tocopherols, tocotrienols, other chroman and side chain derivatives and uses therof
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, (2008/06/13)
The present invention provides an antiproliferative compound having the structural formula wherein X is oxygen, nitrogen or sulfur; R1is alkyl, alkenyl, alkynyl, aryl, heteroaryl, carboxylic acid, carboxylate, carboxamide, ester, thioamide, thiolacid, thiolester, saccharide, alkoxy-linked saccharide, amine, sulfonate, sulfate, phosphate, alcohol, ethers and nitriles; R2is hydrogen, methyl, benzyl carboxylic acid, benzyl carboxylate, benzyl carboxamide, benzylester, saccharide and amine; R3is selected from the group consisting of hydrogen, methyl, benzyl carboxylic acid, benzyl carboxylate, benzyl carboxamide, benzylester, saccharide and amine; R4is of methyl, benzyl carboxylic acid, benzyl carboxylate, benzyl carboxamide, benzylester, saccharide and amine; and R5is alkyl, alkenyl, alkynyl, aryl, heteroaryl, carboxyl, amide and ester. Also provided is a method for inducing apoptosis in a cell comprising administering a composition comprising a compound.
Tocopherols, tocotrienols, other chroman and side chain derivatives and uses thereof
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, (2008/06/13)
The present invention provides an antiproliferative compound having a structural formula where X and Y independently are oxygen, nitrogen or sulfur; R1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, carboxylic acid, carboxylate, carboxamide, est
Certain indole derivatives useful as leukotriene antagonists
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, (2008/06/13)
A compound of the formula STR1 in which R1 is hydrogen, halo, C1-4 alkyl, C1-4 alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C1-4 alkyl, aldehydo, --CH2 Z, --CH=CH--Z or --CH2 CH2 Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R2 is halo, nitrile, an optionally protected acid group or --CONR7 R8 where R7 and R8 are each hydrogen or C1-4 alkyl; R3 and R4 are each hydrogen, C1-4 alkyl, optionally substituted phenyl, or C1-4 alkyl substituted by --CONR7 R8 or an optionally protected acid group; R5 is STR2 where W is --CH=CH--, --CH=N--, --N=CH--, --O-- or --S--, R9 is hydrogen, halo, C1-4 alkyl, C1-4 alkoxy or trihalomethyl, and R10 is hydrogen, C1-4 alkyl, C2-6 alkenyl, C3-6 cycloalkyl or C1-4 alkyl-C3-6 cycloalkyl; R6 is hydrogen or C1-4 alkyl; X is --O--(CH2)n CR11 R12, --CR11 R12 --, --CR11 R12.(CH2)n.CR13 R14 -- or --CR11 =CR12 -- where R11, R12, R13 and R14 are each hydrogen or C1-4 alkyl, and n is 0, 1 or 2; and Y is --O--CR15 R16 --, --CR15 =CR16 -- or --CR15 R16.CR17 R18 -- where R15, R16, R17 and R18 are each hydrogen or C 1-4 alkyl; or a salt thereof. The compounds in unprotected form are active as leukotriene antagonists.
Antitussive and mucus regulating 2-substituted thiazolidines
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, (2008/06/13)
2-Substituted thiazolidines compounds having formula I STR1 wherein X is a CH2, O or S, R is hydroxy or an acyloxy, alkyloxy, alkenyloxy or alkinyloxy group, R1 is hydrogen or a group of formula STR2 R2 is hydrogen or a free or esterified carboxy group, Ra and Rb are hydrogen or methyl, p is zero or 1, R3 is a C1 -C2 alkylsulphonyl group, a phenyl or p-Cl phenyl, p-methylsulphonyl group or an acyl group; are useful as mucus regulating, antitussive and antibronchospastic agents.
1H-NMR- AND MOESSBAUER INVESTIGATIONS ON THE ION PAIRS OF TETRACHLOROFERRATE(III) ANION WITH QUATERNARY PHOSPHONIUM CATIONS
Vincze, L.,Papp, S.
, p. 153 - 162 (2007/10/02)
Paramagnetic ion pairs were investigated by 1H-NMR and Moessbauer spectroscopy in chloroform and dimethyl sulphoxide.It has been shown that the chemical shifts of 1H-NMR peaks arise from a combination of contact and pseudocontact interactions of opposite sign, and the ratio of interactions was definitely influenced by the extent of solvation.On the basis of Moessbauer measurements it was shown that the change of the cation size had an effect on the electron delocalization and symmetry conditions of iron(III) in solid samples, too.In concentrated frozen solutions of ion pairs, different interactions were indicated by Moessbauer spectros copy in chloroform and dimethyl sulphoxide, in accordance with 1H-NMR results.However, in dilute solution such an anion-solvent interaction was observed directly, which could be shown by the NMR method only indirectly.
